Deuterated dimethyl sulfoxide

BPA diglycidyl ether (extent of oligomerization = ∼0.02, physical form = solid), guaiacol (≥ 98% food grade), syringol (99%), vanillyl alcohol (≥ 98%), thioglycolic acid (98%), LiBr (> 99%), LiCl (> 99%), and Amberlyst® 15 hydrogen form (dry) were purchased from Sigma-Aldrich. DA-10 (> 99%) was purchased from TCI. Syringyl alcohol (97%), deuterated dimethyl sulfoxide (DMSO-d₆, ≥99.5%), N,N-dimethylacetamide (DMAc, 99.8+%, HPLC grade), DMSO (anhydrous, 99.7% extra dry), tetrabutylammonium bromide (TBAB, 99+%), epichlorohydrin (99%), and deuterated chloroform (CDCl₃, ≥99.75%) were purchased from acros organics. BPF diglycidyl ether (EPON^TM 862, extent of oligomerization = ∼0.10, physical form = viscous liquid), a product of Hexion, was purchased from Chemical Marketing Concepts Inc. Acetone (≥99.5%), dichloromethane (DCM, ≥99.5%), N,N-dimethylformamide (DMF, ≥99.8%), HCl (36.5 to 38.0% [w/w]), NaOH (≥97%), magnesium sulfate (anhydrous), sodium bicarbonate (≥99.7%), NaCl (≥99.5%), tetrahydrofuran (THF, ≥99%), hexanes (99%), ethyl acetate (≥99.5%), and acetonitrile (≥99.9%) were purchased from Thermo Fisher Scientific. Ar (grade 5), CO₂ (grade 5), and N₂ (grade 5) were purchased from Keen Compressed Gas. All chemicals were used as received except acetone, which was passed through a magnesium sulfate column before use.